


Anti-kink: Anal play

by ash_carpenter



Series: Anti-kink [9]
Category: Supernatural
Genre: Crack, M/M
Language: English
Status: Completed
Published: 2014-03-09
Updated: 2014-03-09
Packaged: 2018-01-15 04:41:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,854
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1291711
Author URL: https://archiveofourown.org/users/ash_carpenter/pseuds/ash_carpenter
Summary: <blockquote class="userstuff">
              <p>Next instalment in my anti-kink series (archived <a href="http://www.livejournal.com/tools/memories.bml?user=ash_carpenter&keyword=Anti-kink&filter=all">here</a> on LJ). I didn't write these in sequence: this is actually their first anti-kink encounter, chronologically speaking. </p>
<p>Okay, so neither of them have tried it before, but it's guaranteed to be amazing, right? According to all the fanfic, anyway.</p>
            </blockquote>





	Anti-kink: Anal play

**Anal play**  
  
  
A lot of things about the sort-of Apocalypse and its aftermath had been unexpected. From the day that Castiel had shown up banging on about raising Dean from perdition to the random Thursday in November when Sam had knocked on Lisa’s door, miraculously back from Lucifer’s cage, things had been generally...odd.  
  
And, considering how their lives had been going up until that point? For anything to seem odd, it actually had to be pretty fucking insane.  
  
However, all of the general unexpectedness had kinda paled into insignificance the day that Sam and Dean had found themselves making out in a graveyard after an easy salt and burn on their first post-apocalyptic hunt together.  
  
As they’d broken away, dazed and flushed, cocks embarrassingly hard, they’d regarded one another with wide eyes.  
  
“Huh.”  
  
“Yeah, didn’t see that one coming.”  
  
Of course, they’d figured out later that they’d probably wanted each other for years, but Dean had been too immersed in the idea of Sam being his snot-nosed kid brother to acknowledge that he was a full-on giant hottie. Whereas Sam had “obviously had his head up his ass” (Dean’s words).  
  
Anyway, in a stunning and unprecedented burst of adult well-adjusted-ness, they’d decided that they were through with self-denial and guilt and repression. They’d soon discovered that they were insanely hot for each other, and it was pretty evident they were never going to love anyone else more or even be capable of a normal relationship, so they’d just gone for it.  
  
Like, really.  
  
Within a week, they were trading heated handjobs in bed and the shower, out back of bars, between library stacks – and, really, anywhere else they could. Soon, blowjobs got thrown into the mix, even though at the beginning they’d both pretty much sucked (and not in the useful way) at giving them. It was a steep learning curve though, and Sam personally thought that Dean’s mouth was so goddamned gorgeous that he’d forgive it for its slightly sloppy technique.  
  
Tangled together in bed not three weeks after their first kiss, naked and humping against one another with increasing desperation, it became obvious that they were ready to progress to the next stage.  
  
Neither of them was a complete stranger to dick, but they were more passing acquaintances than firm friends. Dean hadn’t gone any further than quick and dirty drunken handjobs, and Sam hadn’t had many encounters either, although he _had_ fucked a guy at college a couple of times.  
  
Neither had ever had anything inside their ass (with the exception of an overenthusiastic pretend-nurse’s finger in a psychiatric hospital, which totally didn’t count).  
  
Sam, finding himself on top as they thrust against one another, nudged Dean’s thighs a little wider and trailed his right hand back from its position on Dean’s balls, rubbing it haltingly over his perineum. He looked down to gauge his brother’s reaction, lip caught between his teeth.  
  
“This okay?” he asked breathlessly, stroking the tip of his finger over Dean’s tiny, tight little hole.  
  
Dean squirmed slightly, dick giving an enthusiastic thumbs up, while his pride and self-image protested and muttered, and his brain unhelpfully threw out static and white noise, having offlined completely the moment that Sam had first stuck his tongue in his mouth.  
  
“Uh...” They were both going to be taking a turn at some point, and Dean definitely thought that sex (preferably lots and lots of it) could only improve their relationship, so he had no objection in principle. Plus, all the Supernatural fanfiction he’d secretly been reading assured him that Sam nailing his prostate would be fucking amazing. However, he’d sort of assumed that he’d be on top the first time.  
  
“Why’s that?” panted Sam, and Dean started slightly, wondering how much he’d just said aloud. Fuck, he hoped he hadn’t mentioned the fanfiction thing.  
  
“Yeah, you did.”  
  
Damn it! Stupid fat mouth with no brain filter! Sam’s finger prodding at his ass was very distracting.  
  
“I’m the oldest,” he tried hopefully.  
  
Sam snorted. “I don’t think ‘big brother rules’ apply to incest, Dean.” At Dean’s annoyed pout, Sam dragged their cocks together a little more firmly, the very tip of his finger pushing into Dean just the tiniest bit. “It’s supposed to feel really good,” he ventured. “I’ll be able to press on your prostate and everything’ll feel so intense...”  
  
“If it’s gonna be so awesome, why don’t _you_ go first?” asked Dean gruffly, although he spread his legs wider. “Got lube?” There was no way in hell he was admitting to his brother that the only lubricant he possessed was passion fruit flavoured.  
  
Sam bounded off the bed in a Sasquatch-shaped blur and when he returned in about zero point three seconds, Dean had to wonder when he’d found the time to purchase what looked like a lifetime’s supply of lubricant.  
  
“Pump-action, Sammy? Really?” It looked kinda like the industrial soap dispensers in diner bathrooms. Dean really hoped that wasn’t what it actually was, his mind filling with an image of Sam surreptitiously ripping one off the wall and then hiding it up his shirt. Little freak. “I hope you paid for that.”  
  
Sam grinned. “Nope. Mr. Frederick Botham of New Mexico did. Not sure what his wife’s gonna think when the credit card bill comes through. What with the lube and the dildo, she might have some questions for poor Freddy...”  
  
While Dean would normally have been highly amused, his mind had sort of latched onto the word ‘dildo’ and was backing nervously away from it. “Did you just say dildo?” he asked, mind optimistically hoping that his ears were fucking with it.  
  
“Well yeah,” replied Sam as if it was the most obvious thing in the world. “You want me to put _this_ in you without being stretched out first?”  
  
Dean looked down at Sam’s hard, glistening dick, swallowing a little. He wasn’t entirely sure he wanted Sam putting _that_ in him full stop. Maybe the industrial-sized bottle of lube had been a wise choice after all. Not that he was going to say that, obviously, because acknowledging that your brother had a big cock was an untenable breach of sibling etiquette.  
  
“Get over yourself. You’re not _that_ hung.”  
  
Sam’s eyes narrowed slightly, but he simply said breezily, “Oh, okay then. Guess we can skip the stretching.”  
  
“Wait, what? I didn’t say that!” backtracked Dean, trying to squirm up the bed lest his brother suddenly ram it in unannounced.  
  
“Relax, Dean,” smirked Sam. “I think we should just start slow, with fingers.”  
  
“Yeah, okay,” said Dean warily, some of the tension leaving his frame. He looked at Sam’s hands as he picked up the bottle of lubricant, glaring at his freakishly large fingers. Was it really necessary for him to be so goddamned overgrown?! Still, even his long, thick digits (and, really, it was a wonder he could even tap away on his laptop without punching several keys at once) were a vast improvement on the baseball bat between his legs.  
  
Sam fussed around getting Dean positioned until his brother was growling at him to just get on with it already, and soon Sam’s slick (and _cold_ , the inconsiderate bastard) finger was circling Dean’s entrance.  
  
Dean grunted when he was breached, face scrunching up.  
  
“Does it hurt?”  
  
“No. It’s just...uncomfortable.”  
  
“Uncomfortable how?”  
  
Dean rolled his eyes. “Uncomfortable like someone’s shoved the world’s biggest finger into a passage that’s only really meant to be a one-way system. What did you think, moron?”  
  
“Well, stop fighting me then! Relax.”  
  
“Easy for you to say, Mr. I _Don’t_ Have A Finger Up My Ass.”  
  
“Look, I’m only up to the first knuckle. Bear down.”  
  
“What do you mean, “bear down”?” asked Dean suspiciously, wriggling and hissing. First knuckle? Jesus Christ! He’d been sure that Sam had slipped his whole fist in.  
  
“Uh...Contract your muscles. Like you’re trying to force me out.”  
  
Dean looked at him with mild horror. “No! I’m not a...a...chick in labour or something! Douche. And what if...”  
  
Sam cocked an eyebrow, taking Dean’s distraction as a great opportunity to shove in another inch, making his brother yelp. Ha.  
  
“What if...” A flush was creeping up over Dean’s neck and face. “You know, if I try to force something out and...” He trailed off, cheeks lit up like Christmas.  
  
Sam tried not to laugh at Dean, biting his lip and putting on his serious, concerned face, but he knew his shoulders were shaking by the way that Dean was scowling darkly at him, ears still pink.  
  
“Dean,” he said calmly and reasonably. “Human beings are designed to be able to move and lift in ways that put strain on their muscles. I think if a little muscle contraction was going to make you spontaneously poop yourself, then we’d know about it by now.”  
  
“Shut up!” Dean turned his face into the pillow, hiding it, and tried to push Sam away from him with his foot. “I hate you. Stop laughing at me.”  
  
Sam grinned and leaned down, kissing his ridiculous and adorable brother on his stomach. His entire finger was inside by that point, and he tried wiggling it experimentally, finding that it was still in a vice-like grip.  
  
“Ow!”  
  
“Hurts?”  
  
“No. Feels weird.”  
  
“So why are you saying ‘ow’ then? Big baby.”  
  
“It feels like you’ve poked a dry twig up my ass! Stop messing around and find the fun button already!”  
  
Sam sighed dramatically. “Fine.”  
  
Yeah, fine. Except that Sam only really knew where the prostate was in theory. The times he’d slept with a guy at college, they’d both been drunk and Sam hadn’t really done anything more complicated than point and shoot. However, Sam had fortunately spent some time on Wikipedia looking at diagrams, and the fanfiction he’d also been secretly reading (grateful that he’d hacked Dean’s LJ account and that his brother tended to save the good ones into Memories) was quite instructive.  
  
Sam frowned in concentration, poking around Dean’s front wall. Everything was weirdly both firm and soft at once, and he found himself praying that Dean hurried up and got on board with the whole anal thing because putting his cock in there was going to feel _amazing_.  
  
“Is that it?”  
  
Dean swore as he was unceremoniously jabbed, a sharp stab of pain followed by alien discomfort. “No!”  
  
“Huh, okay.” Sam rooted around a bit more, Dean’s fingers clenching white-knuckled in the sheets and his teeth gritted.  
  
“I wish you’d taken anatomy as one of your ten million classes at Stanford. What the fuck use is Spanish?!”  
  
“You’re right,” Sam agreed drily. “Knowing how to locate my brother’s “fun button” would have been much more useful than speaking another language. Why didn’t I think of that at the time?”  
  
Dean was about to deliver a no-doubt incredibly witty retort, when he felt a mild pulse of something that was vaguely in the vicinity of pleasurable. At least, he thought he did. He grunted and shifted.  
  
“What? Did that feel good?”  
  
Dean shrugged. “It didn’t suck as much as everything else has.”  
  
Despite the not exactly glowing praise, Sam assumed that he must be on the right track. He rubbed the pad of his finger firmly over the same spot, feeling a slightly rounded area when he pressed harder. He’d sort of expected Dean’s back to arch or for him to pant and writhe while letting loose a stream of expletives, but what he got was a scrunched nose and a ‘hmmm’.  
  
“That feels kinda okay,” ventured Dean uncertainly. “Might even be nice if I was hard,” he added pointedly, looking ruefully down at his now flaccid dick. He thought that the odd pressure from his back passage would actually feel good if coupled with the regular kind of stimulation. “You must be near where the prostate is.”  
  
Sam frowned, mentally pulling up a diagram in his head. There was really only one thing the bump he was touching could be, although he had a bit of a fumble around just to be sure there wasn’t a bigger, better bump somewhere. “I, uh, I think that’s it.”  
  
Dean blinked at him. “It? How can that be it? Where the fuck are my fucking fireworks and lightning bolts?!”  
  
“I don’t know!” returned Sam, baffled. He’d been fully expecting to witness the effects of white-hot bursts of intense pleasure, hopefully resulting in Dean immediately spreading his legs and begging to be fucked into the middle of next week. He only had a hazy memory of what it had been like to fuck a man, but he definitely remembered them enjoying themselves. Maybe there was something wrong with Dean? “Perhaps you’re not sensitive enough?”  
  
“Hey, don’t blame me because you can’t get the job done. I bet you’re one of those assholes who blames the girl when he doesn’t manage to make her come during sex!” groused Dean, unreasonably pissed off about his faulty prostate.  
  
“Screw you! I’ve never had any complaints! It’s not my fault you’re...frigid, or something.”  
  
Dean was thoroughly affronted, and was about to express his outrage with a few choice words and possibly some fists, when it occurred to him that he couldn’t feasibly start a fight with his brother when said brother still had a finger wedged up his ass. Besides, it was becoming rapidly clear that fanfiction was the real culprit here. After all, if anal stimulation was really _that_ incredible, everyone would be gay.  
  
“I feel like we’ve been duped.”  
  
“Yeah, I know.” Sam frowned. He should have known that the female-dominated world of fanfic wouldn’t be overly accurate when it came to the inner workings of the male reproductive system. Stupid women.  
  
In defeat, he slumped down on top of Dean, kissing his jaw and idly rubbing their groins together, finger still softly pressing against the spot that had caused so much contention.  
  
Dean murmured contentedly, just happy that his dick was getting attention again. He turned his face toward Sam, latching their mouths together and rolling his hips to rub off against him. Lust returning with a warm surge, Sam went with it, sliding his tongue into Dean’s mouth and rocking against his brother. Soon, they were hard again, Dean unconsciously squeezing Sam between his thighs and positioning himself to allow Sam’s hand room to move, fucking his finger in and out of the slightly loosened passage.  
  
Fireworks, there weren’t. No abrupt spikes of overwhelming bliss emanating from his butt. However, it was still pretty fucking good.  
  
It didn’t take very long before they were shooting all over each other, their spunk a slick mess between their bellies, and after a long kiss Sam rolled off, panting.  
  
Dean hissed as his brother’s finger popped free, the burn almost as bad going out as it was going in. For a brief moment his ass felt all wide and airy, and Dean had a minor flash of panic that his muscles wouldn’t tighten back up and he’d have a flappy back passage for the rest of his life. He was distracted by Sam wiping his finger on the bed sheets, which were unfortunately white.  
  
“Dude! Gross! This is _my_ bed!”  
  
Sam shrugged carelessly. Well, he was hardly gonna wipe essence of Dean’s ass off on his own bed, was he?  
  
Dean had barely finished ranting about how disgusting Sam was when he was startled into silence by the loud, rude sound of a rush of air escaping from his own body. Despite the fact that he had absolutely no problem farting in front of Sam (or anyone, really), it was completely different when the gush of air had been caused by being finger-fucked and he blushed fetchingly.  
  
Sam smirked. “Everything I know about polite etiquette, I learned from my big brother.”  
  
Dean groaned, although he couldn’t help noticing that the humiliating incident had at least made him close back up a little. “This whole gay sex thing is gonna be really undignified, isn’t it?”  
  
“Nah, we’ll figure it out,” reassured Sam.  
  
Muttering something about famous last words, Dean heaved himself off the bed, wincing and cursing as he stood up. His hand flew to his ass and Sam tried to stifle a smug grin.  
  
“Fuck! Man, you are so getting _your_ ass stuffed next time,” groused Dean, waddling toward the bathroom.  
  
“Sure. I’ll give you a couple of hours to recover and then we’ll go again, old man.”  
  
Dean didn’t dignify that comment with anything more than a raised middle finger. Hearing Sam chuckle, he turned and said, “This is the one that’s going in your ass. Bitch.”  
  
Murmuring a perfunctory “jerk”, Sam shuffled around, getting comfortable. Looking at his finger, he pulled a face. “Dean, hurry up! I need to wash my hands.”  
  
“Shoulda thought of that before you messed up my sheets! You’ll have to wait; I think you jarred something loose,” Dean called back, slamming the door as he lifted the lid of the toilet.  
  
Sam scrunched up his face. Maybe Dean had a point about the undignified thing.  
  
Still, things were bound to get easier. Right?  
  
  
  
THE END  



End file.
